The Derby


Soon, though, the race was in trouble again. Just after the turn of the century, the nation was swept up in an antigambling “reform” movement. In 1907 reformers won the Louisville mayorship and promptly banned bookmaking, the only form of wagering at Churchill Downs. Winn was left with two alternatives: antiquated “auction pool” wagering, which excluded bettors of small wagers, and the French pari-mutuel machine, which automatically calculated the winners’ rewards based on what they had wagered, dividing up the total pool of money bet. The latter seemed ideal, eliminating the famous corruption of bookmaking while allowing bets as low as one dollar. But pari-mutuels had had a disappointing history in America; Clark had imported four machines, and like other track operators, he had failed to lure bettors to them. Still, pari-mutuels were the better choice, so Winn opted to use them. City Hall responded by dredging up an ancient law banning machine betting. Winn was left only with auction pools, which would surely be banned also. The Derby and Churchill Downs appeared doomed.

Pondering the looming failure of their race, Winn and the track president, Charlie Grainger, began to wonder how Clark had gained legal authority to use pari-mutuels. They scoured lawbooks and found the answer. Buried deep in the legal code was an amendment excluding pari-mutuels from the antimachine gambling law. “We were jubilant,” Winn later wrote. But with little time before the Derby, he had no pari-mutuels to use. Importation would take too long, and no one knew what had become of Clark’s four machines. Winn recruited an army of Louisvillians to hunt for them; he suspected that City Hall was also searching for the pari-mutuels in hopes of destroying them. Pro-racing hunters found all four, and Winn persuaded a New York track to ship in two abandoned machines. Every one of them was in deplorable condition. Mechanics, working frantically, rebuilt all six.

The crisis still wasn’t over. Learning that Winn had obtained pari-mutuels, City Hall vowed to send the police in to arrest everyone connected to wagering. Winn took the issue to court and won. The Derby was on. Ironically, the clash boosted Derby attendance by flooding the city with publicity. Buoyed by the attention and Winn’s pro- motional fliers, the machines were immensely popular; wagering on the 1908 Derby was five times greater than in 1907. “The machines,” Winn wrote, “had saved racing in Kentucky ...”


Reformism was soon dead, but the Derby was still no more than a local function. Winn needed a headliner, something to break into the national consciousness. In 1913 his wish was answered when an impossible long shot named Donerail dropped from out of the clouds to win the Derby in what remains the race’s greatest shocker. Donerail paid a stunning $184.90 for a $2.00 bet, landing the race in the national news. Seizing the opportunity, Winn traveled back East and turned on the charm, trying to end the quartercentury boycott of his race. In 1915 came the breakthrough: Winn convinced the influential New Yorker Harry Payne Whitney to run his mighty filly Regret in the Derby. Regret simply annihilated the boys, becoming the first filly to win the race. Whitney was euphoric. “I do not care if she never wins another race, or if she never starts in another race,” he said. “She has won the greatest race in America, and I am satisfied.”

With that statement, “the Derby was thus ‘made’ as an American institution,” wrote Winn. Regret “put us over the top.”

The boycott was over, and the Derby prospered, drawing as many as twenty or more world-class horses each year. Winn began courting influential print, and later radio, journalists, treating them to every possible luxury during Derby Week. Drawn by the glowing news coverage, Americans focused on the race each May; by the mid-1920s eighty thousand people were cramming into the track for the race. In 1925 the Derby’s first radio broadcast drew five or six million listeners, an audience estimated to be the largest yet for any broadcast in the history of the medium. By 1931 half the nation was tuning in for the race. With the onset of the Depression, ten state legislatures, desperate for revenue, authorized pari-mutuel betting in order to tax the winnings. Racing quickly became the most heavily attended sport in the nation, and the Derby became its crowning moment.

As the Derby basked in its newfound fame, two other spring races for top three-year-olds, New York’s Belmont Stakes and Maryland’s Preakness Stakes, were also eniovine success. In 1935. when a colt named Omaha achieved the fantastically difficult task of winning all three, writer Charlie Hatton coined the term Triple Crown . What is arguably the most formidable challenge in sports had been born. The two horses that had won all three in earlier years, Sir Barton and Gallant Fox, were retroactively named Triple Crown winners. In 1937 War Admiral became the fourth. No longer an event that would have to stand alone, the Derby now marked the start of a nationally celebrated, weeks-long rite of spring. Winn’s race, hamstrung for so long by political and financial problems, would from now on be defined solely by its spectacular competitors.